The 22 best things to do in Chicago

You'll be blown over by the Windy City's array of activities – from haute cuisine to walking in the sky

Published 24. Apr 2018

Words by Rod O'Connor

The Windy City stands tall among US destinations for its amazing skyline, rich history and a picturesque lakefront that welcomes everyone with open arms. From hanging out with the “Nighthawks” to walking in the air, here are 11 experiences that only a trip to Chicago can deliver.

1. Laugh it up with tomorrow’s comedy stars

From Bill Murray to Tina Fey to Stephen Colbert, Chicago’s comedy scene has served as the springboard for success for countless very funny people. To catch the next generation of comic royalty before they hit the big time on Saturday Night Live, head to Second City, the legendary theater that popularized Chicago’s fast-paced and whip-smart brand of improvised humor.

2. See world-class art in an architectural gem

The Art Institute of Chicago is perhaps most famous for hosting the world’s largest collection of Impressionist paintings outside the Louvre in Paris – including several of Monet’s Water Lilies and Georges Seurat’s massive pointillist masterpiece Sunday Afternoon on La Grande Jatte – 1884. But that’s just the starting point for a museum that you could spend your entire holiday exploring. Iconic American works on display include Edward Hopper’s noir-ish 1942 painting Nighthawks; there’s also a collection of ancient art dating back to 3000BC. Don’t miss the rotating exhibits at the Modern Wing – the thrilling Renzo Piano-designed building that is a work of art in unto itself.

3. Walk in the sky

In the 1890s, Chicago led a building revolution with the invention of the skyscraper – and the city’s skyline has only soared higher since then. There are plenty of places to gawk at the skyline from ground level – but nothing beats getting up there among the tall buildings. For a truly adrenaline-pumping experience, step out onto The Ledge. These glass boxes extend out from the 103rd floor Skydeck of the Willis Tower, the tallest building in the Western Hemisphere, providing jaw-dropping views of up to 50 miles away – and 1,450 feet straight down.

4. Weigh in on the pizza debate

Thin crust or deep pan? New York versus Chicago style pizza is perhaps the greatest of all American food debates. Vote with your stomach at one of the pizza parlors serving up the quintessential, casserole-thick Chicago pies – loaded with gooey mozzarella cheese, spicy Italian sausage, and fresh tomato sauce. You can’t go wrong at Pizzeria Due in River North or one of the many outposts of Lou Malnati’s. But the pie often cited as Chicago’s best is Pequod’s in Lincoln Park, which features a caramelized crust and nontraditional toppings like Italian beef and meatballs.

5. Eat mind-blowing food from a top chef

Chicago’s justly famed for its street food – but if you’re in the mood for something more refined, the city’s fine dining scene is home to some of the world’s best restaurants. Chef Grant Achatz’s Alinea restaurant in Lincoln Park has three Michelin stars to its name, and is consistently in the running for the best restaurant on the planet. If you can’t book a table at Achatz’s flagship haven for experimental cooking, try the more casual Roister in the West Loop. You can order up comfort food dishes like whole chicken and leg of lamb – and watch the chefs cook them in an open hearth, right in front of you.

6. Bike the lakefront

Forward-thinking city leaders designated more than 20 miles of prime Chicago lakefront as public land way back in the early 1900s. To this day, residents and visitors enjoy free access to scenic beaches and winding bike paths that stretch the length of the city. Do as the locals do and cruise the Chicago Lakefront Trail on one of the light-blue Divvy bikes from Chicago’s easy-to-use bike-sharing program. For less than ten bucks, you can take unlimited 30-minute rides for an entire day.

7. Ride a recreation of the original Ferris wheel

In 1893, Chicago burst onto the global stage with the World’s Columbian Exposition, a monumental event that featured everything from replicas of Christopher Columbus’ ships to the world’s first Ferris Wheel. The White City may be long gone – and Ferris’ creation with it – but Chicago still has a wheel to call its own. At Navy Pier, the popular 34-acre tourist attraction that juts out into Lake Michigan, the Centennial Wheel is an ode to the original ride. At 196-foot-high, it’s 60 feet shorter than Ferris’ original – but what it lacks in height it makes up for in modern amenities such as air-conditioned gondolas and high-tech safety glass. (Photo by Fineas Anton on Unsplash)

8. Visit the old ballpark

Wrigley Field, Major League Baseball’s second-oldest stadium, was hallowed ground even before the Chicago Cubs won their first World Series title in 108 years in 2016. Now, it’s the center of the baseball universe. During the season, there’s nothing quite like sitting in the bleachers with the hardcore Cub fans. But a look at the famous marquee is worth a visit any time of year – as is a visit to the brand-new Park at Wrigley, a 50,000-square-foot outdoor plaza. As well as restaurants and a Cubs merchandise store, there are also plenty of events throughout the year, including free outdoor cinema screenings – and HITT fitness events, if you’re feeling energetic. (Photo by Shelby L Bell licensed under CC BY 2.0)

9. Walk in Al Capone’s footsteps

In 1920, the Eighteenth Amendment made alcohol illegal across the United States – creating a black market where bootleggers and mobsters thrived. Chicago became the heart of an industrial-scale criminal enterprise where gangsters like Al Capone, Hymie Weiss and Dean O’Bannion ruled the streets. The best way to learn about the history of the city’s Prohibition era is to book an Untouchable Tour, hosted by guides dressed in period garb – their tales of mobster exploits take in former speakeasies, the church where Capone prayed, and sites of notorious events like the St. Valentine’s Day Massacre.

10. Pose in front of “the bean”

Score a one-of-kind selfie at Cloud Gate, a giant interactive sculpture crafted by British artist Anish Kapoor that’s become the centerpiece of the Loop. The centerpiece of Millennium Park, a 24.5-acre public space in the middle of downtown on Chicago’s lakefront, “the bean” gets its charming nickname from its unmistakably legume-like shape. Its 168 polished stainless steel plates form a seamless surface reflecting the Chicago skyline – and the crowds looking for that perfect Instagram snap – in a distorted funhouse mirror.

11. Sing the blues in the “blues capital”

When the Great Migration of Southern African-Americans reached the industrial cities of the North beginning in the early 1900s, musicians in Chicago began popularizing a raw, electric style of the roots music from the South: the blues. Today, the Windy City is known as the blues capital of the world – and is the only place where you can see icons like guitarist Buddy Guy on a small stage in his own club, Buddy Guy’s Legends. Rosa’s Lounge in Logan Square and Kingston Mines in Lincoln Park are grittier neighborhood venues that consistently showcase top-notch acts.

12. Venture into a “living urban canvas"

One block west of the Michigan Avenue tourist drag is the Wabash Arts Corridor – a “living urban canvas” of larger-than-life public artwork. Stroll along Wabash Avenue, from Van Buran Street to Roosevelt Road, and you’ll discover more than two dozen colorful murals and thought-provoking installations that have transformed the previously ho-hum industrial buildings of the South Loop neighbourhood.

13. Chow down on gourmet Mexican food

Many visitors are unaware that Chicago is home to a huge Mexican population – and that the city has an embarrassment of riches when it comes to traditional south-of-the-border cuisine. Distinctive regional flavors can be found on both ends of the spectrum. Start with a simply delicious taco at one of the joints that line 18th Street in Pilsen (try Carnitas Don Pedro for their legendary, slowly simmered pork). Then, go upscale with a soulful and elegant multi-course dinner at Topolobampo – the four-star restaurant in River North from famed chef Rick Bayless, who has long championed Mexican cooking at restaurants such as Frontera Grill. (Photo by vxla licensed under CC BY 2.0)

14. Go tropical in a tiki bar

Tucked away amidst the bustle of Chicago’s busiest neighborhoods are eclectic cocktail havens that transport you to a tropical paradise – a welcome respite from the Windy City’s breezes. Logan Square’s Lost Lake, from internationally recognized mixologist Paul McGee, specializes in meticulously crafted specialty daiquiris and punches. Closer to downtown, Three Dots and a Dash in River North serves its creations in fanciful glassware shaped like skulls and sea urchins.

15. Head out of the city to Starved Rock State Park

A little more than an hour’s drive from downtown Chicago is one of the Midwest’s most stunning natural landscapes: Starved Rock State Park. Hike along a 13-mile path overlooking the Illinois River and discover spectacular waterfalls, more than 18 different canyons, and majestic wildlife including white-tail fawn and bald eagles.

16. Take a tour with The Devil in the White City

This spine-tingling tour is inspired by author Erik Larson’s bestselling history of the 1893 World’s Columbian Exhibition – and the serial killer who preyed on its visitors. Led by experts from the Chicago Architecture Museum, it takes in the south side locations and landmarks featured in the book, including the home of Fair critic Ida B. Wells, the Midway and the site of the former fairgrounds in Jackson Park.

17. Catch the Bard’s works at Chicago Shakespeare Theater

While Chicago is known for its edgy storefront theater scene, many tourists stroll right past the Chicago Shakespeare Theater – a beacon of culture smack dab in the middle of the crowded commercial zone on Navy Pier. The state-of-the-art space presents both traditional and modern interpretations of Bard classics on two stages, along with works from Beckett, Shaw, and other legendary playwrights.

18. Enjoy a taste of Sweden

Once boasting the largest concentration of Swedes outside of Stockholm, Chicago’s North Side Andersonville neighborhood still proudly wears its Scandinavian heritage on its blue-and-yellow sleeve. Visit the Swedish American Museum to learn the story behind Swedish immigration to Chicago. Then, stop in at Svea, a charming café serving authentic Scandinavian treats: belt-busting pancakes, traditional Limpa bread (sweet Swedish rye) and, of course, meatballs doused in rich gravy.

19. Explore the landscapes of the world under glass

Garfield Park Conservatory is one of Chicago’s best-kept secrets – one of the largest greenhouse conservatories in the USA, it brings eye-popping greens and rare specimens from around the world to Chicago’s West Side. Its eight rooms were designed in the early 1900s as “landscape art under glass” – a series of botanical environments showcasing thousands of plant species, from tropical flora to botanical treasures from the Midwestern prairieland.

20. Discover Frank Lloyd Wright’s Robie House

Hidden away in Hyde Park on the University of Chicago’s campus is an architectural gem from the early 20th century. The Robie House, built in 1910, is considered the best example of architect and designer Frank Lloyd Wright’s revolutionary Prairie style – so it’s no surprise that it’s been designated a National Historic Landmark. Tours of the house, which features Wright’s signature horizontal lines and low-pitched roofs, provide a peek inside the mind of a master of American architecture. (Photo by Teemu008 licensed under CC BY-SA 2.0)

21. Be illuminated under the world’s largest Tiffany glass dome

Inside the stately Chicago Cultural Center, just across Michigan Avenue from Millennium Park, is a 10,000-square-foot glass mosaic dome that is thought to be the largest of its kind. The kaleidoscope of more than 30,000 individual panes of colored glass embedded in ornate iron framing is well worth a quick visit – if for no other reason than to ponder what an estimated $35 million worth of glassware looks like.

22. Uncover the history of surgery

The fascinating International Museum of Surgical Science is a glittering paean to the complex history of surgery and specialized medicine – and even many of Chicago’s own residents aren’t aware of its existence. Housed in an historic Lincoln Park mansion styled after a Versailles chateau, its exhibits highlight everything from Roman surgical tools and a reconstructed 19th century dentist’s office, to modern art with medical motifs. Its extensive library includes rare, early medical texts and journals from pioneers such as Florence Nightingale.